JP2005535657A5 - - Google Patents
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- JP2005535657A5 JP2005535657A5 JP2004519699A JP2004519699A JP2005535657A5 JP 2005535657 A5 JP2005535657 A5 JP 2005535657A5 JP 2004519699 A JP2004519699 A JP 2004519699A JP 2004519699 A JP2004519699 A JP 2004519699A JP 2005535657 A5 JP2005535657 A5 JP 2005535657A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- phenyl
- benzenesulfonamide
- methylsulfonyl
- benzopyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 chromene compound Chemical class 0.000 claims 56
- 239000000203 mixture Substances 0.000 claims 42
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims 30
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 30
- 229940124639 Selective inhibitor Drugs 0.000 claims 30
- 239000000651 prodrug Substances 0.000 claims 25
- 229940002612 prodrug Drugs 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 25
- 239000003814 drug Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 206010053648 Vascular occlusion Diseases 0.000 claims 11
- 208000021331 vascular occlusion disease Diseases 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 102000001938 Plasminogen Activators Human genes 0.000 claims 8
- 239000003527 fibrinolytic agent Substances 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 229940127126 plasminogen activator Drugs 0.000 claims 8
- 229960000103 thrombolytic agent Drugs 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 108010001014 Plasminogen Activators Proteins 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 claims 6
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 229960000187 tissue plasminogen activator Drugs 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 208000010125 myocardial infarction Diseases 0.000 claims 4
- ZFKBWSREWJOSSJ-VIFPVBQESA-N (2s)-6,8-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2O[C@H](C(F)(F)F)C(C(=O)O)=CC2=C1 ZFKBWSREWJOSSJ-VIFPVBQESA-N 0.000 claims 3
- IWTSTYWGRNOWJQ-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzo[f]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(C=C(C(C(=O)O)O3)C(F)(F)F)C3=CC=C21 IWTSTYWGRNOWJQ-UHFFFAOYSA-N 0.000 claims 3
- QGCKNIAMHUUUDI-UHFFFAOYSA-N 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C(C)(C)C)C(Cl)=C2 QGCKNIAMHUUUDI-UHFFFAOYSA-N 0.000 claims 3
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims 3
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims 3
- 208000031481 Pathologic Constriction Diseases 0.000 claims 3
- 239000003146 anticoagulant agent Substances 0.000 claims 3
- 229940127219 anticoagulant drug Drugs 0.000 claims 3
- 229940127218 antiplatelet drug Drugs 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 208000037804 stenosis Diseases 0.000 claims 3
- 230000036262 stenosis Effects 0.000 claims 3
- ZJOUYQCSZYKGKU-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 ZJOUYQCSZYKGKU-UHFFFAOYSA-N 0.000 claims 2
- NSRMOHFGSWCCFK-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CN=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 NSRMOHFGSWCCFK-UHFFFAOYSA-N 0.000 claims 2
- NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 0.000 claims 2
- UJSFKTUZOASIPA-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 UJSFKTUZOASIPA-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- XCTHXVRBSIHBAC-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound ClC1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 XCTHXVRBSIHBAC-UHFFFAOYSA-N 0.000 claims 2
- NONBXOPYDWLZGR-UHFFFAOYSA-N 6-chloro-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C NONBXOPYDWLZGR-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 2
- 201000000057 Coronary Stenosis Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 206010002906 aortic stenosis Diseases 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001562 benzopyrans Chemical class 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 230000000747 cardiac effect Effects 0.000 claims 2
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 2
- LWIFWMYFVZYWMS-UHFFFAOYSA-N 1,2-difluoro-3-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=C(F)C=CC=2)F)CCC1 LWIFWMYFVZYWMS-UHFFFAOYSA-N 0.000 claims 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims 1
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims 1
- RFPZMXMBYMEQHZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC=C1C1=CC=C(F)C=C1 RFPZMXMBYMEQHZ-UHFFFAOYSA-N 0.000 claims 1
- GWMFOHRUWPDLIP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-phenyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 GWMFOHRUWPDLIP-UHFFFAOYSA-N 0.000 claims 1
- HUVCBGHNHBHJBX-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1C(C)(C)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 HUVCBGHNHBHJBX-UHFFFAOYSA-N 0.000 claims 1
- MBUIIOVYVHAZOU-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)cyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CCC1 MBUIIOVYVHAZOU-UHFFFAOYSA-N 0.000 claims 1
- SZHKSRZKPUOAGO-UHFFFAOYSA-N 1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CCC1 SZHKSRZKPUOAGO-UHFFFAOYSA-N 0.000 claims 1
- BPWDIXPFAHESAF-UHFFFAOYSA-N 1-[3,3-dimethyl-5-(4-methylsulfonylphenyl)cyclopenta-1,4-dien-1-yl]-4-fluorobenzene Chemical compound C=1C(C)(C)C=C(C=2C=CC(F)=CC=2)C=1C1=CC=C(S(C)(=O)=O)C=C1 BPWDIXPFAHESAF-UHFFFAOYSA-N 0.000 claims 1
- VKUCTHVTLJBHDT-UHFFFAOYSA-N 1-[4,4-dimethyl-2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-fluorobenzene Chemical compound C1C(C)(C)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 VKUCTHVTLJBHDT-UHFFFAOYSA-N 0.000 claims 1
- XKSNSSNGFIQSFK-UHFFFAOYSA-N 1-ethyl-4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)C=1N(CC)N=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(F)C=C1 XKSNSSNGFIQSFK-UHFFFAOYSA-N 0.000 claims 1
- RAUHMMADXJJVRP-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 RAUHMMADXJJVRP-UHFFFAOYSA-N 0.000 claims 1
- JQDLRYPRLMZWFM-UHFFFAOYSA-N 1-methylsulfanyl-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 JQDLRYPRLMZWFM-UHFFFAOYSA-N 0.000 claims 1
- 125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 0.000 claims 1
- KSFMAASFLCWROX-UHFFFAOYSA-N 2,4-dichloro-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)CCC1 KSFMAASFLCWROX-UHFFFAOYSA-N 0.000 claims 1
- VCLNQQUCGTWUKD-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C(=CC=CC=2)Cl)S1 VCLNQQUCGTWUKD-UHFFFAOYSA-N 0.000 claims 1
- NWVGCEQIXKQQPS-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)=NC(C(F)(F)F)=C1 NWVGCEQIXKQQPS-UHFFFAOYSA-N 0.000 claims 1
- SOOKCKQNOCMHPV-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C=C(Cl)C(F)=CC=2)S1 SOOKCKQNOCMHPV-UHFFFAOYSA-N 0.000 claims 1
- YLFBPUKBMRJHLM-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(Cl)C=CC=2)=NC(C(F)(F)F)=C1 YLFBPUKBMRJHLM-UHFFFAOYSA-N 0.000 claims 1
- UFSJAWLGOHKVBH-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=C(F)C(OC)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 UFSJAWLGOHKVBH-UHFFFAOYSA-N 0.000 claims 1
- MEAMLMDMYOLDGW-UHFFFAOYSA-N 2-(3-fluoro-5-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC(F)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 MEAMLMDMYOLDGW-UHFFFAOYSA-N 0.000 claims 1
- RSABMOYFBOLDLO-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RSABMOYFBOLDLO-UHFFFAOYSA-N 0.000 claims 1
- ZZBKFGAUXXMYNA-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-phenylimidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC=CC=2)=C1 ZZBKFGAUXXMYNA-UHFFFAOYSA-N 0.000 claims 1
- UPXZCQZUZDWZHE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(F)=CC=2)=C1 UPXZCQZUZDWZHE-UHFFFAOYSA-N 0.000 claims 1
- RIZFWOPNUQFLEF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1-(4-methylsulfonylphenyl)imidazole Chemical compound N=1C(C)=CN(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(Cl)C=C1 RIZFWOPNUQFLEF-UHFFFAOYSA-N 0.000 claims 1
- PEUVGLHBVHFKPT-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 PEUVGLHBVHFKPT-UHFFFAOYSA-N 0.000 claims 1
- KCPPTAVUOWTXDZ-UHFFFAOYSA-N 2-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2N=CC=CC=2)=NC(C(F)(F)F)=C1 KCPPTAVUOWTXDZ-UHFFFAOYSA-N 0.000 claims 1
- AGCRHVNIFLDQNI-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazol-2-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(CC(O)=O)O1 AGCRHVNIFLDQNI-UHFFFAOYSA-N 0.000 claims 1
- NECDCTAHUMBLQG-UHFFFAOYSA-N 2-bromo-6-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=C(Br)N=C1C1=CC=C(F)C=C1 NECDCTAHUMBLQG-UHFFFAOYSA-N 0.000 claims 1
- KYNAWJZJGXEMMS-UHFFFAOYSA-N 2-chloro-1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 KYNAWJZJGXEMMS-UHFFFAOYSA-N 0.000 claims 1
- ZTHDILTXFNKYMK-UHFFFAOYSA-N 2-methyl-4-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 ZTHDILTXFNKYMK-UHFFFAOYSA-N 0.000 claims 1
- TZUKXDRCVJCLLL-UHFFFAOYSA-N 2-methyl-5-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 TZUKXDRCVJCLLL-UHFFFAOYSA-N 0.000 claims 1
- UJAMUMWHXRVKDM-UHFFFAOYSA-N 2-methyl-6-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 UJAMUMWHXRVKDM-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- ZACVSMBOYXVARY-UHFFFAOYSA-N 6-(methylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)NC)=CC=C21 ZACVSMBOYXVARY-UHFFFAOYSA-N 0.000 claims 1
- MQSZXCIMIPOLLQ-UHFFFAOYSA-N 6-(tert-butylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)NC(C)(C)C)=CC=C21 MQSZXCIMIPOLLQ-UHFFFAOYSA-N 0.000 claims 1
- CSOISVJKLBMNCK-UHFFFAOYSA-N 6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 CSOISVJKLBMNCK-UHFFFAOYSA-N 0.000 claims 1
- MOYKDFAFGUWTQO-UHFFFAOYSA-N 6-benzylsulfonyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)CC1=CC=CC=C1 MOYKDFAFGUWTQO-UHFFFAOYSA-N 0.000 claims 1
- OODLETPYKNYFPC-UHFFFAOYSA-N 6-bromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 OODLETPYKNYFPC-UHFFFAOYSA-N 0.000 claims 1
- QFRDGIZQIJYOJO-UHFFFAOYSA-N 6-bromo-3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-2-(trifluoromethyl)pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(Br)=NC(C(F)(F)F)=C1C1=CC=C(F)C=C1 QFRDGIZQIJYOJO-UHFFFAOYSA-N 0.000 claims 1
- BSCFTYXHRKRJKJ-UHFFFAOYSA-N 6-bromo-8-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 BSCFTYXHRKRJKJ-UHFFFAOYSA-N 0.000 claims 1
- WTTFVQCIUHZESW-UHFFFAOYSA-N 6-bromo-8-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Br)C=C2OC WTTFVQCIUHZESW-UHFFFAOYSA-N 0.000 claims 1
- VEENGDJNDWZTOU-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 VEENGDJNDWZTOU-UHFFFAOYSA-N 0.000 claims 1
- FIGFIPYZSNLSOF-UHFFFAOYSA-N 6-chloro-7-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(CC)C(Cl)=C2 FIGFIPYZSNLSOF-UHFFFAOYSA-N 0.000 claims 1
- ZQRBVSGXWNRTHN-UHFFFAOYSA-N 6-chloro-7-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C)C(Cl)=C2 ZQRBVSGXWNRTHN-UHFFFAOYSA-N 0.000 claims 1
- ARTWTAYIQKFKNP-UHFFFAOYSA-N 6-chloro-7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1C1=CC=CC=C1 ARTWTAYIQKFKNP-UHFFFAOYSA-N 0.000 claims 1
- QBEGCKDFGWDVKY-UHFFFAOYSA-N 6-chloro-8-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2CC QBEGCKDFGWDVKY-UHFFFAOYSA-N 0.000 claims 1
- CUHYRNMEWAAFPL-UHFFFAOYSA-N 6-chloro-8-fluoro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(F)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 CUHYRNMEWAAFPL-UHFFFAOYSA-N 0.000 claims 1
- CBMIVBLNFVXYHN-UHFFFAOYSA-N 6-chloro-8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C(C)C CBMIVBLNFVXYHN-UHFFFAOYSA-N 0.000 claims 1
- XGONYOLEZPFZPF-UHFFFAOYSA-N 6-ethoxy-3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-2-(trifluoromethyl)pyridine Chemical compound C=1C=C(F)C=CC=1C=1C(C(F)(F)F)=NC(OCC)=CC=1C1=CC=C(S(C)(=O)=O)C=C1 XGONYOLEZPFZPF-UHFFFAOYSA-N 0.000 claims 1
- YKJCXFQLAGEPJU-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound IC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 YKJCXFQLAGEPJU-UHFFFAOYSA-N 0.000 claims 1
- WRXXEGPVSCGBRF-UHFFFAOYSA-N 6-methylsulfonyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)C)=CC=C21 WRXXEGPVSCGBRF-UHFFFAOYSA-N 0.000 claims 1
- ZVWOGLMGGCMZOF-UHFFFAOYSA-N 7,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(C)C(C)=CC=C21 ZVWOGLMGGCMZOF-UHFFFAOYSA-N 0.000 claims 1
- ABNPGORLVYQTCX-UHFFFAOYSA-N 7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 ABNPGORLVYQTCX-UHFFFAOYSA-N 0.000 claims 1
- QVCOFXANOXVCSG-UHFFFAOYSA-N 7-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(C(C)C)=CC=C21 QVCOFXANOXVCSG-UHFFFAOYSA-N 0.000 claims 1
- UGQHPBVUJSRYTD-UHFFFAOYSA-N 7-tert-butyl-2-(1,1,2,2,2-pentafluoroethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)C(F)(F)F)OC2=CC(C(C)(C)C)=CC=C21 UGQHPBVUJSRYTD-UHFFFAOYSA-N 0.000 claims 1
- MFIJXIQKTVUZEM-UHFFFAOYSA-N 7-tert-butyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(C(C)(C)C)=CC=C21 MFIJXIQKTVUZEM-UHFFFAOYSA-N 0.000 claims 1
- HWHWDSNSWIQJMF-UHFFFAOYSA-N 8-bromo-5-fluoro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1F HWHWDSNSWIQJMF-UHFFFAOYSA-N 0.000 claims 1
- RJXCLTHZNZATCO-UHFFFAOYSA-N 8-bromo-6-fluoro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 RJXCLTHZNZATCO-UHFFFAOYSA-N 0.000 claims 1
- RUSILFUVBUFONF-UHFFFAOYSA-N 8-bromo-6-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(Br)=C21 RUSILFUVBUFONF-UHFFFAOYSA-N 0.000 claims 1
- ZIGWRQKLXXGWHR-UHFFFAOYSA-N 8-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ZIGWRQKLXXGWHR-UHFFFAOYSA-N 0.000 claims 1
- GPVVLCXEWPYEAF-UHFFFAOYSA-N 8-chloro-5,6-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C(C)C(C)=CC(Cl)=C21 GPVVLCXEWPYEAF-UHFFFAOYSA-N 0.000 claims 1
- JPWVMGPBBNJBBV-UHFFFAOYSA-N 8-chloro-6-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(OC)=CC(Cl)=C21 JPWVMGPBBNJBBV-UHFFFAOYSA-N 0.000 claims 1
- DIUCLSCBUOAEQY-UHFFFAOYSA-N 8-chloro-6-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(Cl)=C21 DIUCLSCBUOAEQY-UHFFFAOYSA-N 0.000 claims 1
- JTYJBUOQGLXJEC-UHFFFAOYSA-N 8-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC=CC=1C1=CC=CC=C1 JTYJBUOQGLXJEC-UHFFFAOYSA-N 0.000 claims 1
- VZXWQKOBWHFICH-UHFFFAOYSA-N 8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=CC=C2C(C)C VZXWQKOBWHFICH-UHFFFAOYSA-N 0.000 claims 1
- 108010058207 Anistreplase Proteins 0.000 claims 1
- 208000003017 Aortic Valve Stenosis Diseases 0.000 claims 1
- OJFXXRGUVBEGSD-UHFFFAOYSA-N C(C)(=O)OCC(CC1=CC=CC=C1)C=1OC(=C(N1)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C Chemical compound C(C)(=O)OCC(CC1=CC=CC=C1)C=1OC(=C(N1)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C OJFXXRGUVBEGSD-UHFFFAOYSA-N 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 claims 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims 1
- 101000605403 Homo sapiens Plasminogen Proteins 0.000 claims 1
- ANMATWQYLIFGOK-UHFFFAOYSA-N Iguratimod Chemical compound CS(=O)(=O)NC1=CC=2OC=C(NC=O)C(=O)C=2C=C1OC1=CC=CC=C1 ANMATWQYLIFGOK-UHFFFAOYSA-N 0.000 claims 1
- GJGZQTGPOKPFES-UHFFFAOYSA-N SC-57666 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)CCC1 GJGZQTGPOKPFES-UHFFFAOYSA-N 0.000 claims 1
- JHBIMJKLBUMNAU-UHFFFAOYSA-N SC-58125 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 JHBIMJKLBUMNAU-UHFFFAOYSA-N 0.000 claims 1
- 108010023197 Streptokinase Proteins 0.000 claims 1
- 108010039185 Tenecteplase Proteins 0.000 claims 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims 1
- YKEMJELQYOBDCY-UHFFFAOYSA-N [Na].FC1=C(C=CC(=C1)F)SC1=C(C=C2C=CC(C2=C1)=O)NS(=O)(=O)C Chemical compound [Na].FC1=C(C=CC(=C1)F)SC1=C(C=C2C=CC(C2=C1)=O)NS(=O)(=O)C YKEMJELQYOBDCY-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 229960003318 alteplase Drugs 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 229960000983 anistreplase Drugs 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000006003 dichloroethyl group Chemical group 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- 125000006001 difluoroethyl group Chemical group 0.000 claims 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229940125672 glycoprotein IIb/IIIa inhibitor Drugs 0.000 claims 1
- 229960002897 heparin Drugs 0.000 claims 1
- 229920000669 heparin Polymers 0.000 claims 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- TTZNQDOUNXBMJV-UHFFFAOYSA-N mavacoxib Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 TTZNQDOUNXBMJV-UHFFFAOYSA-N 0.000 claims 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims 1
- HKYOGYJVZLWKLN-UHFFFAOYSA-N n-[5-(3,4-difluorophenyl)-2-(trifluoromethyl)-1,3-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1C1=C(NS(=O)(=O)C=2C=CC=CC=2)N=C(C(F)(F)F)O1 HKYOGYJVZLWKLN-UHFFFAOYSA-N 0.000 claims 1
- YVLDKYLEHKIHOK-UHFFFAOYSA-N n-[5-(4-fluorophenyl)sulfanylthiophen-2-yl]methanesulfonamide Chemical compound S1C(NS(=O)(=O)C)=CC=C1SC1=CC=C(F)C=C1 YVLDKYLEHKIHOK-UHFFFAOYSA-N 0.000 claims 1
- CXJONBHNIJFARE-UHFFFAOYSA-N n-[6-(2,4-difluorophenoxy)-1-oxo-2,3-dihydroinden-5-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2CCC(=O)C=2C=C1OC1=CC=C(F)C=C1F CXJONBHNIJFARE-UHFFFAOYSA-N 0.000 claims 1
- HCSFFMYIHYYVTK-UHFFFAOYSA-N n-benzyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(NCC=2C=CC=CC=2)S1 HCSFFMYIHYYVTK-UHFFFAOYSA-N 0.000 claims 1
- 229960000965 nimesulide Drugs 0.000 claims 1
- 125000004999 nitroaryl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 1
- 208000009138 pulmonary valve stenosis Diseases 0.000 claims 1
- 208000030390 pulmonic stenosis Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229960002917 reteplase Drugs 0.000 claims 1
- 108010051412 reteplase Proteins 0.000 claims 1
- 229960005202 streptokinase Drugs 0.000 claims 1
- 229960000216 tenecteplase Drugs 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 229960005356 urokinase Drugs 0.000 claims 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims 1
- 229960005080 warfarin Drugs 0.000 claims 1
Claims (68)
式中、Gは、O、S又はNRaであり;
ここでRaは、アルキルであり;
式中、R1は、H及びアリールからなる群より選択され;
式中、R2は、カルボキシル、アミノカルボニル、アルキルスルホニルアミノカルボニル及びアルコキシカルボニルからなる群より選択され;
式中、R3は、アルキルチオ、ニトロ及びアルキルスルホニルより選択される1以上の基で随意に置換される、ハロアルキル、アルキル、アラルキル、シクロアルキル及びアリールからなる群より選択され;そして
式中、それぞれのR4は、独立して、H、ハロ、アルキル、アラルキル、アルコキシ、アリールオキシ、ヘテロアリールオキシ、アラルキルオキシ、ヘテロアラルキルオキシ、ハロアルキル、ハロアルコキシ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロアリールアミノ、ヘテロアリールアルキルアミノ、ニトロ、アミノ、アミノスルホニル、アルキルアミノスルホニル、アリールアミノスルホニル、ヘテロアリールアミノスルホニル、アラルキルアミノスルホニル、ヘテロアラルキルアミノスルホニル、ヘテロシクロスルホニル、アルキルスルホニル、ヒドロキシアリールカルボニル、ニトロアリール、随意に置換されるアリール、随意に置換されるヘテロアリール、アラルキルカルボニル、ヘテロアリールカルボニル、アリールカルボニル、アミノカルボニル、及びアルキルカルボニルからなる群より選択され;
式中、R4は、それが付く炭素原子と環Eの残りと一緒にナフチル基を形成する]
の化合物、又はその製剤的に許容される塩又は異性体又はプロドラッグを含む、請求項1の組成物。 The cyclooxygenase-2 selective inhibitor has the formula:
Where G is O, S or NR a ;
Where R a is alkyl;
Wherein R 1 is selected from the group consisting of H and aryl;
Wherein R 2 is selected from the group consisting of carboxyl, aminocarbonyl, alkylsulfonylaminocarbonyl and alkoxycarbonyl;
Wherein R 3 is selected from the group consisting of haloalkyl, alkyl, aralkyl, cycloalkyl and aryl, optionally substituted with one or more groups selected from alkylthio, nitro and alkylsulfonyl; and R 4 is independently H, halo, alkyl, aralkyl, alkoxy, aryloxy, heteroaryloxy, aralkyloxy, heteroaralkyloxy, haloalkyl, haloalkoxy, alkylamino, arylamino, aralkylamino, heteroarylamino Heteroarylalkylamino, nitro, amino, aminosulfonyl, alkylaminosulfonyl, arylaminosulfonyl, heteroarylaminosulfonyl, aralkylaminosulfonyl, heteroaralkylaminosulfonyl, Selected from the group consisting of rocyclosulfonyl, alkylsulfonyl, hydroxyarylcarbonyl, nitroaryl, optionally substituted aryl, optionally substituted heteroaryl, aralkylcarbonyl, heteroarylcarbonyl, arylcarbonyl, aminocarbonyl, and alkylcarbonyl Is;
In which R 4 together with the carbon atom to which it is attached and the remainder of ring E form a naphthyl group]
Or a pharmaceutically acceptable salt or isomer or prodrug thereof.
Gが、O、S又はNRbであり;
R1がHであり;
Rbがアルキルであり;
R2が、カルボキシル、アミノカルボニル、アルキルスルホニルアミノカルボニル及びアルコキシカルボニルからなる群より選択され;
R3が、ハロアルキル、アルキル、アラルキル、シクロアルキル及びアリールからなる群より選択され、ここでハロアルキル、アルキル、アラルキル、シクロアルキル及びアリールは、それぞれ独立して、アルキルチオ、ニトロ及びアルキルスルホニルからなる群より選択される1以上の基で随意に置換され;そして
それぞれのR4が、独立して、ヒドリド、ハロ、アルキル、アラルキル、アルコキシ、アリールオキシ、ヘテロアリールオキシ、アラルキルオキシ、ヘテロアラルキルオキシ、ハロアルキル、ハロアルコキシ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロアリールアミノ、ヘテロアリールアルキルアミノ、ニトロ、アミノ、アミノスルホニル、アルキルアミノスルホニル、アリールアミノスルホニル、ヘテロアリールアミノスルホニル、アラルキルアミノスルホニル、ヘテロアラルキルアミノスルホニル、ヘテロシクロスルホニル、アルキルスルホニル、随意に置換されるアリール、随意に置換されるヘテロアリール、アラルキルカルボニル、ヘテロアリールカルボニル、アリールカルボニル、アミノカルボニル、及びアルキルカルボニルからなる群より選択されるか;又は、R4が環Eと一緒にナフチル基を形成する、請求項10の組成物。 n is an integer of 0, 1, 2, 3 or 4;
G is O, S or NR b ;
R 1 is H;
R b is alkyl;
R 2 is selected from the group consisting of carboxyl, aminocarbonyl, alkylsulfonylaminocarbonyl and alkoxycarbonyl;
R 3 is selected from the group consisting of haloalkyl, alkyl, aralkyl, cycloalkyl and aryl, wherein haloalkyl, alkyl, aralkyl, cycloalkyl and aryl are each independently from the group consisting of alkylthio, nitro and alkylsulfonyl. Optionally substituted with one or more selected groups; and each R 4 is independently hydrido, halo, alkyl, aralkyl, alkoxy, aryloxy, heteroaryloxy, aralkyloxy, heteroaralkyloxy, haloalkyl, Haloalkoxy, alkylamino, arylamino, aralkylamino, heteroarylamino, heteroarylalkylamino, nitro, amino, aminosulfonyl, alkylaminosulfonyl, arylaminosulfonyl, hete Arylaminosulfonyl, aralkylaminosulfonyl, heteroaralkylaminosulfonyl, heterocyclosulfonyl, alkylsulfonyl, optionally substituted aryl, optionally substituted heteroaryl, aralkylcarbonyl, heteroarylcarbonyl, arylcarbonyl, aminocarbonyl, and alkyl or it is selected from the group consisting of carbonyl; or, R 4 to form a naphthyl group together with the ring E, the composition of claim 10.
Gが、酸素又はイオウであり;
R1がHであり;
R2が、カルボキシル、低級アルキル、低級アラルキル又は低級アルコキシカルボニルであり;
R3が、低級ハロアルキル、低級シクロアルキル又はフェニルであり;そして
それぞれのR4が、H、ハロ、低級アルキル、低級アルコキシ、低級ハロアルキル、低級ハロアルコキシ、低級アルキルアミノ、ニトロ、アミノ、アミノスルホニル、低級アルキルアミノスルホニル、5員のヘテロアリールアルキルアミノスルホニル、6員のヘテロアリールアルキルアミノスルホニル、低級アラルキルアミノスルホニル、5員の窒素含有ヘテロシクロスルホニル、6員の窒素含有ヘテロシクロスルホニル、低級アルキルスルホニル、随意に置換されるフェニル、低級アラルキルカルボニル、又は低級アルキルカルボニルであるか;又は、
R4は、それが付く炭素原子と環Eの残りと一緒にナフチル基を形成する、請求項10の組成物。 n is an integer of 0, 1, 2, 3 or 4;
G is oxygen or sulfur;
R 1 is H;
R 2 is carboxyl, lower alkyl, lower aralkyl or lower alkoxycarbonyl;
R 3 is lower haloalkyl, lower cycloalkyl or phenyl; and each R 4 is H, halo, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, lower alkylamino, nitro, amino, aminosulfonyl, Lower alkylaminosulfonyl, 5 membered heteroarylalkylaminosulfonyl, 6 membered heteroarylalkylaminosulfonyl, lower aralkylaminosulfonyl, 5 membered nitrogen containing heterocyclosulfonyl, 6 membered nitrogen containing heterocyclosulfonyl, lower alkylsulfonyl, Optionally substituted phenyl, lower aralkylcarbonyl, or lower alkylcarbonyl; or
R 4 is, it forms a naphthyl group together with the rest of the carbon atoms and the ring E stick composition of claim 10.
R3が低級ハロアルキルであり;そして
それぞれのR4が、H、ハロ、低級アルキル、低級ハロアルキル、低級ハロアルコキシ、低級アルキルアミノ、アミノ、アミノスルホニル、低級アルキルアミノスルホニル、5員のヘテロアリールアルキルアミノスルホニル、6員のヘテロアリールアルキルアミノスルホニル、低級アラルキルアミノスルホニル、低級アルキルスルホニル、6員の窒素含有ヘテロシクロスルホニル、随意に置換されるフェニル、低級アラルキルカルボニル、又は低級アルキルカルボニルであるか;又は、R4は、環Eと一緒にナフチル基を形成する、請求項10の組成物。 R 2 is carboxyl;
R 3 is lower haloalkyl; and each R 4 is H, halo, lower alkyl, lower haloalkyl, lower haloalkoxy, lower alkylamino, amino, aminosulfonyl, lower alkylaminosulfonyl, 5-membered heteroarylalkylamino Sulfonyl, 6-membered heteroarylalkylaminosulfonyl, lower aralkylaminosulfonyl, lower alkylsulfonyl, 6-membered nitrogen-containing heterocyclosulfonyl, optionally substituted phenyl, lower aralkylcarbonyl, or lower alkylcarbonyl; or The composition of claim 10, wherein R 4 together with ring E forms a naphthyl group.
R3が、フルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、ペンタフルオロエチル、ヘプタフルオロプロピル、ジフルオロエチル、ジフルオロプロピル、ジクロロエチル、ジクロロプロピル、ジフルオロメチル、又はトリフルオロメチルであり;そして
それぞれのR4が、H、クロロ、フルオロ、ブロモ、ヨード、メチル、エチル、イソプロピル、tert−ブチル、ブチル、イソブチル、ペンチル、ヘキシル、メトキシ、エトキシ、イソプロピルオキシ、tert−ブチルオキシ、トリフルオロメチル、ジフルオロメチル、トリフルオロメトキシ、アミノ、N,N−ジメチルアミノ、N,N−ジエチルアミノ、N−フェニルメチルアミノスルホニル、N−フェニルエチルアミノスルホニル、N−(2−フリルメチル)アミノスルホニル、ニトロ、N,N−ジメチルアミノスルホニル、アミノスルホニル、N−メチルアミノスルホニル、N−エチルスルホニル、2,2−ジメチルエチルアミノスルホニル、N,N−ジメチルアミノスルホニル、N−(2−メチルプロピル)アミノスルホニル、N−モルホリノスルホニル、メチルスルホニル、ベンジルカルボニル、2,2−ジメチルプロピルカルボニル、フェニルアセチル又はフェニルであるか;又は、
R4は、それが付く炭素原子と環Eの残りと一緒にナフチル基を形成する、請求項10の組成物。 n is an integer of 0, 1, 2, 3 or 4;
R 3 is fluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, difluoromethyl, or trifluoromethyl; and the respective R 4 is H, chloro, fluoro, bromo, iodo, methyl, ethyl, isopropyl, tert-butyl, butyl, isobutyl, pentyl, hexyl, methoxy, ethoxy, isopropyloxy, tert-butyloxy, trifluoromethyl, difluoromethyl, tri Fluoromethoxy, amino, N, N-dimethylamino, N, N-diethylamino, N-phenylmethylaminosulfonyl, N-phenylethylaminosulfonyl, N- (2-furylmethyl) Minosulfonyl, nitro, N, N-dimethylaminosulfonyl, aminosulfonyl, N-methylaminosulfonyl, N-ethylsulfonyl, 2,2-dimethylethylaminosulfonyl, N, N-dimethylaminosulfonyl, N- (2-methyl Propyl) aminosulfonyl, N-morpholinosulfonyl, methylsulfonyl, benzylcarbonyl, 2,2-dimethylpropylcarbonyl, phenylacetyl or phenyl; or
R 4 is, it forms a naphthyl group together with the rest of the carbon atoms and the ring E stick composition of claim 10.
R8は、トリフルオロメチル又はペンタフルオロエチルであり;
R9は、H、クロロ、又はフルオロであり;
R10は、H、クロロ、ブロモ、フルオロ、ヨード、メチル、tert−ブチル、トリフルオロメトキシ、メトキシ、ベンジルカルボニル、ジメチルアミノスルホニル、イソプロピルアミノスルホニル、メチルアミノスルホニル、ベンジルアミノスルホニル、フェニルエチルアミノスルホニル、メチルプロピルアミノスルホニル、メチルスルホニル、又はモルホリノスルホニルであり;
R11は、H、メチル、エチル、イソプロピル、tert−ブチル、クロロ、メトキシ、ジエチルアミノ、又はフェニルであり;そして
R12は、H、クロロ、ブロモ、フルオロ、メチル、エチル、tert−ブチル、メトキシ、又はフェニルである]の化合物を含む、請求項10の組成物。 The cyclooxygenase-2 selective inhibitor has the formula:
R 8 is trifluoromethyl or pentafluoroethyl;
R 9 is H, chloro, or fluoro;
R 10 is H, chloro, bromo, fluoro, iodo, methyl, tert-butyl, trifluoromethoxy, methoxy, benzylcarbonyl, dimethylaminosulfonyl, isopropylaminosulfonyl, methylaminosulfonyl, benzylaminosulfonyl, phenylethylaminosulfonyl, Methylpropylaminosulfonyl, methylsulfonyl, or morpholinosulfonyl;
R 11 is H, methyl, ethyl, isopropyl, tert-butyl, chloro, methoxy, diethylamino, or phenyl; and R 12 is H, chloro, bromo, fluoro, methyl, ethyl, tert-butyl, methoxy, Or a phenyl] compound of claim 10.
6−クロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−7−メチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−(1−メチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−7−(1,1−ジメチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−8−(1−メチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
2−トリフルオロメチル−3H−ナフトピラン−3−カルボン酸;
7−(1,1−ジメチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−ブロモ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−クロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−トリフルオロメトキシ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
5,7−ジクロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−フェニル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
7,8−ジメチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6,8−ビス(ジメチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
7−(1−メチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
7−フェニル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−7−エチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−8−エチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−7−フェニル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6,7−ジクロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6,8−ジクロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
2−トリフルオロメチル−3H−ナフト[2,1−b]ピラン−3−カルボン酸;
6−クロロ−8−メチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−クロロ−6−メチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−クロロ−6−メトキシ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−ブロモ−8−クロロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−ブロモ−6−フルオロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−ブロモ−6−メチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−ブロモ−5−フルオロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−8−フルオロ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−ブロモ−8−メトキシ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[[(フェニルメチル)アミノ]スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[(ジメチルアミノ)スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[(メチルアミノ)スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[(4−モルホリノ)スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[(1,1−ジメチルエチル)アミノスルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[(2−メチルプロピル)アミノスルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−メチルスルホニル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−クロロ−6−[[(フェニルメチル)アミノ]スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−フェニルアセチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6,8−ジブロモ−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
8−クロロ−5,6−ジメチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6,8−ジクロロ−(S)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−ベンジルスルホニル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[[N−(2−フリルメチル)アミノ]スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−[[N−(2−フェニルエチル)アミノ]スルホニル]−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−ヨード−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
7−(1,1−ジメチルエチル)−2−ペンタフルオロエチル−2H−1−ベンゾピラン−3−カルボン酸;及び
6−クロロ−2−トリフルオロメチル−2H−1−ベンゾチオピラン−3−カルボン酸
からなる群より選択される、請求項10の組成物。 A cyclooxygenase-2 selective inhibitor, pharmaceutically acceptable salt, isomer or prodrug thereof:
6-chloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-7-methyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8- (1-methylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-7- (1,1-dimethylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-8- (1-methylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
2-trifluoromethyl-3H-naphthopyran-3-carboxylic acid;
7- (1,1-dimethylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-bromo-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-chloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-trifluoromethoxy-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
5,7-dichloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-phenyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
7,8-dimethyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6,8-bis (dimethylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
7- (1-methylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
7-phenyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-7-ethyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-8-ethyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-7-phenyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6,7-dichloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6,8-dichloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
2-trifluoromethyl-3H-naphtho [2,1-b] pyran-3-carboxylic acid;
6-chloro-8-methyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-chloro-6-methyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-chloro-6-methoxy-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-bromo-8-chloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-bromo-6-fluoro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-bromo-6-methyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-bromo-5-fluoro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-8-fluoro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-bromo-8-methoxy-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[[(Phenylmethyl) amino] sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[(dimethylamino) sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[(methylamino) sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[(4-morpholino) sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[(1,1-dimethylethyl) aminosulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[(2-methylpropyl) aminosulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-methylsulfonyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-chloro-6-[[(phenylmethyl) amino] sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-phenylacetyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6,8-dibromo-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
8-chloro-5,6-dimethyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6,8-dichloro- (S) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-benzylsulfonyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[[N- (2-furylmethyl) amino] sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-[[N- (2-phenylethyl) amino] sulfonyl] -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-iodo-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
From 7- (1,1-dimethylethyl) -2-pentafluoroethyl-2H-1-benzopyran-3-carboxylic acid; and 6-chloro-2-trifluoromethyl-2H-1-benzothiopyran-3-carboxylic acid 12. The composition of claim 10, wherein the composition is selected from the group consisting of:
式中、R1は、ヘテロシクリル、シクロアルキル、シクロアルケニル及びアリールからなる群より選択され、ここでR1は、置換可能な位置で、アルキル、ハロアルキル、シアノ、カルボキシル、アルコキシカルボニル、ヒドロキシル、ヒドロキシアルキル、ハロアルコキシ、アミノ、アルキルアミノ、アリールアミノ、ニトロ、アルコキシアルキル、アルキルスルフィニル、ハロ、アルコキシ及びアルキルチオより選択される1以上の基で随意に置換され;
式中、R2は、メチル又はアミノからなる群より選択され;そして
式中、R3は、H、ハロ、アルキル、アルケニル、アルキニル、オキソ、シアノ、カルボキシル、シアノアルキル、ヘテロシクリルオキシ、アルキルオキシ、アルキルチオ、アルキルカルボニル、シクロアルキル、アリール、ハロアルキル、ヘテロシクリル、シクロアルケニル、アラルキル、ヘテロシクリルアルキル、アシル、アルキルチオアルキル、ヒドロキシアルキル、アルコキシカルボニル、アリールカルボニル、アラルキルカルボニル、アラルケニル、アルコキシアルキル、アリールチオアルキル、アリールオキシアルキル、アラルキルチオアルキル、アラルコキシアルキル、アルコキシアラルコキシアルキル、アルコキシカルボニルアルキル、アミノカルボニル、アミノカルボニルアルキル、アルキルアミノカルボニル、N−アリールアミノカルボニル、N−アルキル−N−アリールアミノカルボニル、アルキルアミノカルボニルアルキル、カルボキシアルキル、アルキルアミノ、N−アリールアミノ、N−アラルキルアミノ、N−アルキル−N−アラルキルアミノ、N−アルキル−N−アリールアミノ、アミノアルキル、アルキルアミノアルキル、N−アリールアミノアルキル、N−アラルキルアミノアルキル、N−アルキル−N−アラルキルアミノアルキル、N−アルキル−N−アリールアミノアルキル、アリールオキシ、アラルコキシ、アリールチオ、アラルキルチオ、アルキルスルフィニル、アルキルスルホニル、アミノスルホニル、アルキルアミノスルホニル、N−アリールアミノスルホニル、アリールスルホニル、N−アルキル−N−アリールアミノスルホニルより選択される基からなる群より選択される]の化合物、又はその製剤的に許容される塩若しくはプロドラッグを含む、請求項1の組成物。 The cyclooxygenase inhibitor has the formula:
Wherein R 1 is selected from the group consisting of heterocyclyl, cycloalkyl, cycloalkenyl and aryl, wherein R 1 is alkyl, haloalkyl, cyano, carboxyl, alkoxycarbonyl, hydroxyl, hydroxyalkyl at a substitutable position. Optionally substituted with one or more groups selected from haloalkoxy, amino, alkylamino, arylamino, nitro, alkoxyalkyl, alkylsulfinyl, halo, alkoxy and alkylthio;
Wherein R 2 is selected from the group consisting of methyl or amino; and wherein R 3 is H, halo, alkyl, alkenyl, alkynyl, oxo, cyano, carboxyl, cyanoalkyl, heterocyclyloxy, alkyloxy, Alkylthio, alkylcarbonyl, cycloalkyl, aryl, haloalkyl, heterocyclyl, cycloalkenyl, aralkyl, heterocyclylalkyl, acyl, alkylthioalkyl, hydroxyalkyl, alkoxycarbonyl, arylcarbonyl, aralkylcarbonyl, aralkenyl, alkoxyalkyl, arylthioalkyl, aryloxy Alkyl, aralkylthioalkyl, aralkoxyalkyl, alkoxyaralkoxyalkyl, alkoxycarbonylalkyl, aminocarbonyl Aminocarbonylalkyl, alkylaminocarbonyl, N-arylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, alkylaminocarbonylalkyl, carboxyalkyl, alkylamino, N-arylamino, N-aralkylamino, N-alkyl-N -Aralkylamino, N-alkyl-N-arylamino, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-aralkylaminoalkyl, N-alkyl-N-aralkylaminoalkyl, N-alkyl-N-arylamino Alkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, alkylaminosulfonyl, N-arylaminosulfonate Or a pharmaceutically acceptable salt or prodrug thereof; or a pharmaceutically acceptable salt or prodrug thereof; or a compound selected from the group consisting of: .
R16は、メチル又はエチルであり;
R17は、クロロ又はフルオロであり;
R18は、水素又はフルオロであり;
R19は、水素、フルオロ、クロロ、メチル、エチル、メトキシ、エトキシ又はヒドロキシであり;
R20は、水素又はフルオロであり;
R21は、クロロ、フルオロ、トリフルオロメチル又はメチルである、
但し、R17、R18、R19及びR20は、R16がエチルであり、R19がHであるとき、すべてがフルオロではない]の化合物、又はその異性体、製剤的に許容される塩、エステル、又はプロドラッグを含む、請求項1の組成物。 The cyclooxygenase-2 selective inhibitor has the formula:
R 16 is methyl or ethyl;
R 17 is chloro or fluoro;
R 18 is hydrogen or fluoro;
R 19 is hydrogen, fluoro, chloro, methyl, ethyl, methoxy, ethoxy or hydroxy;
R 20 is hydrogen or fluoro;
R 21 is chloro, fluoro, trifluoromethyl or methyl,
Provided that R 17 , R 18 , R 19 and R 20 are not all fluoro when R 16 is ethyl and R 19 is H, or isomers thereof, and pharmaceutically acceptable. 2. The composition of claim 1, comprising a salt, ester, or prodrug.
R17とR19がクロロであり;
R18とR20が水素であり;そして
R21がメチルである、請求項31の組成物。 R 16 is ethyl;
R 17 and R 19 are chloro;
R 18 and R 20 is hydrogen; and R 21 is methyl A composition according to claim 31.
R17がフルオロであり;
R18、R19及びR20が水素であり;そして
R21がクロロである、請求項31の組成物。 R 16 is methyl;
R 17 is fluoro;
32. The composition of claim 31, wherein R <18> , R <19> and R < 20 > are hydrogen; and R < 21 > is chloro.
Xは、O又はSであり;
Jは、炭素環又は複素環であり;
R22は、NHSO2CH3又はFであり;
R23は、H、NO2、又はFであり;そして
R24は、H、NHSO2CH3、又は(SO2CH3)C6H4である]の化合物、又はその異性体、製剤的に許容される塩、エステル、又はプロドラッグを含む、請求項1の組成物。 The cyclooxygenase-2 selective inhibitor has the formula:
X is O or S;
J is a carbocyclic or heterocyclic ring;
R 22 is NHSO 2 CH 3 or F;
R 23 is H, NO 2 , or F; and R 24 is H, NHSO 2 CH 3 , or (SO 2 CH 3 ) C 6 H 4 ], or an isomer, pharmaceutical The composition of claim 1 comprising an acceptable salt, ester, or prodrug.
TとMは、独立して、フェニル、ナフチル、5〜6員を含んでなり、1〜4のヘテロ原子を保有する複素環に由来する基、又は3〜7の炭素原子を有する飽和炭化水素環に由来する基であり;
Q1、Q2、L1又はL2は、独立して、水素、ハロゲン、1〜6の炭素原子を有する低級アルキル、トリフルオロメチル、又は1〜6の炭素原子を有する低級メトキシであり;そして
Q1、Q2、L1又はL2の少なくとも1つはパラ位にあり、−S(O)n−R{ここでnは、0、1、又は2であり、Rは、1〜6の炭素原子を有する低級アルキル基、又は1〜6の炭素原子を有する低級ハロアルキル基である}、又は−SO2NH2であるか;又は
Q1及びQ2は、メチレンジオキシであるか;又は
L1及びL2は、メチレンジオキシであり;そして
R25、R26、R27、及びR28は、独立して、水素、ハロゲン、1〜6の炭素原子を有する低級アルキル基、1〜6の炭素原子を有する低級ハロアルキル基、又はフェニル、ナフチル、チエニル、フリル及びピリジルからなる群より選択される芳香族基であるか;又は
R25及びR26はOであるか;又は
R27及びR28はOであるか;又は
R25、R26は、それらが付く炭素原子と一緒に3〜7の炭素原子を有する飽和炭化水素環を形成するか;又は
R27、R28は、それらが付く炭素原子と一緒に3〜7の炭素原子を有する飽和炭化水素環を形成する]の化合物、又はその異性体、製剤的に許容される塩、エステル、又はプロドラッグを含む、請求項1の組成物。 The cyclooxygenase-2 selective inhibitor has the formula:
T and M are independently phenyl, naphthyl, a group derived from a heterocyclic ring containing 5 to 6 members and having 1 to 4 heteroatoms, or a saturated hydrocarbon having 3 to 7 carbon atoms A group derived from a ring;
Q 1 , Q 2 , L 1 or L 2 are independently hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, trifluoromethyl, or lower methoxy having 1 to 6 carbon atoms; And at least one of Q 1 , Q 2 , L 1 or L 2 is in the para position, and —S (O) n —R {where n is 0, 1, or 2; Are lower alkyl groups having 6 carbon atoms, or lower haloalkyl groups having 1 to 6 carbon atoms}, or —SO 2 NH 2 ; or are Q 1 and Q 2 methylenedioxy? Or L 1 and L 2 are methylenedioxy; and R 25 , R 26 , R 27 , and R 28 are independently hydrogen, halogen, a lower alkyl group having 1 to 6 carbon atoms, Lower haloalkyl having 1 to 6 carbon atoms Or phenyl, naphthyl, thienyl, or an aromatic group selected from the group consisting of furyl and pyridyl; or R 25 and R 26 are either O; or R 27 and R 28 is O; or R 25 and R 26 together with the carbon atom to which they are attached form a saturated hydrocarbon ring having from 3 to 7 carbon atoms; or R 27 and R 28 are together with the carbon atom to which they are attached 3 to 3 Or a isomer, pharmaceutically acceptable salt, ester, or prodrug thereof. 7. The composition of claim 1 wherein the compound forms a saturated hydrocarbon ring having 7 carbon atoms.
3−[(3−クロロ−フェニル)−(4−メタンスルホニル−フェニル)−メチレン]−ジヒドロ−フラン−2−オン;
8−アセチル−3−(4−フルオロフェニル)−2−(4−メチルスルホニル)フェニル−イミダゾ(1,2−a);
5,5−ジメチル−4−(4−メチルスルホニル)フェニル−3−フェニル−2−(5H)−フラノン;
5−(4−フルオロフェニル)−1−[4−(メチルスルホニル)フェニル]−3−(トリフルオロメチル)ピラゾール;
4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]−1−フェニル−3−(トリフルオロメチル)ピラゾール;
4−(5−(4−クロロフェニル)−3−(4−メトキシフェニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(3,5−ビス(4−メチルフェニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(5−(4−クロロフェニル)−3−フェニル−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(3,5−ビス(4−メトキシフェニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(5−(4−クロロフェニル)−3−(4−メチルフェニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(5−(4−クロロフェニル)−3−(4−ニトロフェニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(5−(4−クロロフェニル)−3−(5−クロロ−2−チエニル)−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−(4−クロロ−3,5−ジフェニル−1H−ピラゾール−1−イル)ベンゼンスルホンアミド;
4−[5−(4−クロロフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−フェニル−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−フルオロフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−メトキシフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−クロロフェニル)−3−(ジフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−メチルフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[4−クロロ−5−(4−クロロフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[3−(ジフルオロメチル)−5−(4−メチルフェニル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[3−(ジフルオロメチル)−5−フェニル−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[3−(ジフルオロメチル)−5−(4−メトキシフェニル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[3−シアノ−5−(4−フルオロフェニル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[3−(ジフルオロメチル)−5−(3−フルオロ−4−メトキシフェニル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(3−フルオロ−4−メトキシフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[4−クロロ−5−フェニル−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−クロロフェニル)−3−(ヒドロキシメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−(N,N−ジメチルアミノ)フェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
5−(4−フルオロフェニル)−6−[4−(メチルスルホニル)フェニル]スピロ[2.4]ヘプト−5−エン;
4−[6−(4−フルオロフェニル)スピロ[2.4]ヘプト−5−エン−5−イル]ベンゼンスルホンアミド;
6−(4−フルオロフェニル)−7−[4−(メチルスルホニル)フェニル]スピロ[3.4]オクト−6−エン;
5−(3−クロロ−4−メトキシフェニル)−6−[4−(メチルスルホニル)フェニル]スピロ[2.4]ヘプト−5−エン;
4−[6−(3−クロロ−4−メトキシフェニル)スピロ[2.4]ヘプト−5−エン−5−イル]ベンゼンスルホンアミド;
5−(3,5−ジクロロ−4−メトキシフェニル)−6−[4−(メチルスルホニル)フェニル]スピロ[2.4]ヘプト−5−エン;
5−(3−クロロ−4−フルオロフェニル)−6−[4−(メチルスルホニル)フェニル]スピロ[2.4]ヘプト−5−エン;
4−[6−(3,4−ジクロロフェニル)スピロ[2.4]ヘプト−5−エン−5−イル]ベンゼンスルホンアミド;
2−(3−クロロ−4−フルオロフェニル)−4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)チアゾール;
2−(2−クロロフェニル)−4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)チアゾール;
5−(4−フルオロフェニル)−4−(4−メチルスルホニルフェニル)−2−メチルチアゾール;
4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)−2−トリフルオロメチルチアゾール;
4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)−2−(2−チエニル)チアゾール;
4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)−2−ベンジルアミノチアゾール;
4−(4−フルオロフェニル)−5−(4−メチルスルホニルフェニル)−2−(1−プロピルアミノ)チアゾール;
2−[(3,5−ジクロロフェノキシ)メチル−4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]チアゾール;
5−(4−フルオロフェニル)−4−(4−メチルスルホニルフェニル)−2−トリフルオロメチルチアゾール;
1−メチルスルホニル−4−[1,1−ジメチル−4−(4−フルオロフェニル)シクロペンタ−2,4−ジエン−3−イル]ベンゼン;
4−[4−(4−フルオロフェニル)−1,1−ジメチルシクロペンタ−2,4−ジエン−3−イル]ベンゼンスルホンアミド;
5−(4−フルオロフェニル)−6−[4−(メチルスルホニル)フェニル]スピロ[2.4]ヘプタ−4,6−ジエン;
4−[6−(4−フルオロフェニル)スピロ[2.4]ヘプタ−4,6−ジエン−5−イル]ベンゼンスルホンアミド;
6−(4−フルオロフェニル)−2−メトキシ−5−[4−(メチルスルホニル)フェニル]−ピリジン−3−カルボニトリル;
2−ブロモ−6−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]−ピリジン−3−カルボニトリル;
6−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]−2−フェニル−ピリジン−3−カルボニトリル;
4−[2−(4−メチルピリジン−2−イル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
4−[2−(5−メチルピリジン−3−イル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
4−[2−(2−メチルピリジン−3−イル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
3−[1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール−2−イル]ピリジン;
2−[1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール−2−イル]ピリジン;
2−メチル−4−[1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール−2−イル]ピリジン;
2−メチル−6−[1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール−2−イル]ピリジン;
4−[2−(6−メチルピリジン−3−イル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
2−(3,4−ジフルオロフェニル)−1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール;
4−[2−(4−メチルフェニル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
2−(4−クロロフェニル)−1−[4−(メチルスルホニル)フェニル]−4−メチル−1H−イミダゾール;
2−(4−クロロフェニル)−1−[4−(メチルスルホニル)フェニル]−4−フェニル−1H−イミダゾール;
2−(4−クロロフェニル)−4−(4−フルオロフェニル)−1−[4−(メチルスルホニル)フェニル]−1H−イミダゾール;
2−(3−フルオロ−4−メトキシフェニル)−1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール;
1−[4−(メチルスルホニル)フェニル]−2−フェニル−4−トリフルオロメチル−1H−イミダゾール;
2−(4−メチルフェニル)−1−[4−(メチルスルホニル)フェニル]−4−トリフルオロメチル−1H−イミダゾール;
4−[2−(3−クロロ−4−メチルフェニル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
2−(3−フルオロ−5−メチルフェニル)−1−[4−(メチルスルホニル)フェニル]−4−(トリフルオロメチル)−1H−イミダゾール;
4−[2−(3−フルオロ−5−メチルフェニル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
2−(3−メチルフェニル)−1−[4−(メチルスルホニル)フェニル]−4−トリフルオロメチル−1H−イミダゾール;
4−[2−(3−メチルフェニル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
1−[4−(メチルスルホニル)フェニル]−2−(3−クロロフェニル)−4−トリフルオロメチル−1H−イミダゾール;
4−[2−(3−クロロフェニル)−4−トリフルオロメチル−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
4−[2−フェニル−4−トリフルオロメチル−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
4−[2−(4−メトキシ−3−クロロフェニル)−4−トリフルオロメチル−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
1−アリル−4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−5−(トリフルオロメチル)−1H−ピラゾール;
4−[1−エチル−4−(4−フルオロフェニル)−5−(トリフルオロメチル)−1H−ピラゾール−3−イル]ベンゼンスルホンアミド;
N−フェニル−[4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−5−(トリフルオロメチル)−1H−ピラゾール−1−イル]アセトアミド;
[4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−5−(トリフルオロメチル)−1H−ピラゾール−1−イル]酢酸エチル;
4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−1−(2−フェニルエチル)−1H−ピラゾール;
4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−1−(2−フェニルエチル)−5−(トリフルオロメチル)ピラゾール;
1−エチル−4−(4−フルオロフェニル)−3−[4−(メチルスルホニル)フェニル]−5−(トリフルオロメチル)−1H−ピラゾール;
5−(4−フルオロフェニル)−4−(4−メチルスルホニルフェニル)−2−トリフルオロメチル−1H−イミダゾール;
4−[4−(メチルスルホニル)フェニル]−5−(2−チオフェニル)−2−(トリフルオロメチル)−1H−イミダゾール;
5−(4−フルオロフェニル)−2−メトキシ−4−[4−(メチルスルホニル)フェニル]−6−(トリフルオロメチル)ピリジン;
2−エトキシ−5−(4−フルオロフェニル)−4−[4−(メチルスルホニル)フェニル]−6−(トリフルオロメチル)ピリジン;
5−(4−フルオロフェニル)−4−[4−(メチルスルホニル)フェニル]−2−(2−プロピニルオキシ)−6−(トリフルオロメチル)ピリジン;
2−ブロモ−5−(4−フルオロフェニル)−4−[4−(メチルスルホニル)フェニル]−6−(トリフルオロメチル)ピリジン;
4−[2−(3−クロロ−4−メトキシフェニル)−4,5−ジフルオロフェニル]ベンゼンスルホンアミド;
1−(4−フルオロフェニル)−2−[4−(メチルスルホニル)フェニル]ベンゼン;
5−ジフルオロメチル−4−(4−メチルスルホニルフェニル)−3−フェニルイソオキサゾール;
4−[3−エチル−5−フェニルイソオキサゾール−4−イル]ベンゼンスルホンアミド;
4−[5−ジフルオロメチル−3−フェニルイソオキサゾール−4−イル]ベンゼンスルホンアミド;
4−[5−ヒドロキシメチル−3−フェニルイソオキサゾール−4−イル]ベンゼンスルホンアミド;
4−[5−メチル−3−フェニル−イソオキサゾール−4−イル]ベンゼンスルホンアミド;
1−[2−(4−フルオロフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(4−フルオロ−2−メチルフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(4−クロロフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(2,4−ジクロロフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(4−トリフルオロメチルフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(4−メチルチオフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(4−フルオロフェニル)−4,4−ジメチルシクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
4−[2−(4−フルオロフェニル)−4,4−ジメチルシクロペンテン−1−イル]ベンゼンスルホンアミド;
1−[2−(4−クロロフェニル)−4,4−ジメチルシクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
4−[2−(4−クロロフェニル)−4,4−ジメチルシクロペンテン−1−イル]ベンゼンスルホンアミド;
4−[2−(4−フルオロフェニル)シクロペンテン−1−イル]ベンゼンスルホンアミド;
4−[2−(4−クロロフェニル)シクロペンテン−1−イル]ベンゼンスルホンアミド;
1−[2−(4−メトキシフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
1−[2−(2,3−ジフルオロフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
4−[2−(3−フルオロ−4−メトキシフェニル)シクロペンテン−1−イル]ベンゼンスルホンアミド;
1−[2−(3−クロロ−4−メトキシフェニル)シクロペンテン−1−イル]−4−(メチルスルホニル)ベンゼン;
4−[2−(3−クロロ−4−フルオロフェニル)シクロペンテン−1−イル]ベンゼンスルホンアミド;
4−[2−(2−メチルピリジン−5−イル)シクロペンテン−1−イル]ベンゼンスルホンアミド;
2−[4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]オキサゾール−2−イル]−2−ベンジル−酢酸エチル;
2−[4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]オキサゾール−2−イル]酢酸;
2−(tert−ブチル)−4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]オキサゾール;
4−(4−フルオロフェニル)−5−[4−(メチルスルホニル)フェニル]−2−フェニルオキサゾール;
4−(4−フルオロフェニル)−2−メチル−5−[4−(メチルスルホニル)フェニル]オキサゾール;
4−[5−(3−フルオロ−4−メトキシフェニル)−2−トリフルオロメチル−4−オキサゾリル]ベンゼンスルホンアミド;
6−クロロ−7−(1,1−ジメチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
6−クロロ−8−メチル−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;
5,5−ジメチル−3−(3−フルオロフェニル)−4−メチルスルホニル−2(5H)−フラノン;
6−クロロ−2−トリフルオロメチル−2H−1−ベンゾチオピラン−3−カルボン酸;
4−[5−(4−クロロフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(4−メチルフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
4−[5−(3−フルオロ−4−メトキシフェニル)−3−(ジフルオロメチル)−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
3−[1−[4−(メチルスルホニル)フェニル]−4−トリフルオロメチル−1H−イミダゾール−2−イル]ピリジン;
2−メチル−5−[1−[4−(メチルスルホニル)フェニル]−4−トリフルオロメチル−1H−イミダゾール−2−イル]ピリジン;
4−[2−(5−メチルピリジン−3−イル)−4−(トリフルオロメチル)−1H−イミダゾール−1−イル]ベンゼンスルホンアミド;
4−[5−メチル−3−フェニルイソオキサゾール−4−イル]ベンゼンスルホンアミド;
4−[5−ヒドロキシメチル−3−フェニルイソオキサゾール−4−イル]ベンゼンスルホンアミド;
[2−トリフルオロメチル−5−(3,4−ジフルオロフェニル)−4−オキサゾリル]ベンゼンスルホンアミド;
4−[2−メチル−4−フェニル−5−オキサゾリル]ベンゼンスルホンアミド;
4−[5−(2−フルオロ−4−メトキシフェニル)−2−トリフルオロメチル−4−オキサゾリル]ベンゼンスルホンアミド;
[2−(2−クロロ−6−フルオロ−フェニルアミノ)−5−メチル−フェニル]−酢酸;
N−(4−ニトロ−2−フェノキシ−フェニル)−メタンスルホンアミド又はニメスリド;
N−[6−(2,4−ジフルオロ−フェノキシ)−1−オキソ−インダン−5−イル]−メタンスルホンアミド;
N−[6−(2,4−ジフルオロ−フェニルスルファニル)−1−オキソ−1H−インデン−5−イル]−メタンスルホンアミド・ナトリウム塩;
N−[5−(4−フルオロ−フェニルスルファニル)−チオフェン−2−イル]−メタンスルホンアミド;
3−(3,4−ジフルオロ−フェノキシ)−4−(4−メタンスルホニル−フェニル)−5−メチル−5−(2,2,2−トリフルオロエチル)−5H−フラン−2−オン;
(5Z)−2−アミノ−5−[[3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチレン−4(5H)−チアゾロン;
N−[3−(ホルミルアミノ)−4−オキソ−6−フェノキシ−4H−1−ベンゾピラン−7−イル]−メタンスルホンアミド;
(6aR,10aR)−3−(1,1−ジメチルヘプチル)−6a,7,10,10a−テトラヒドロ−1−ヒドロキシ−6,6−ジメチル−6H−ジベンゾ[b,d]ピラン−9−カルボン酸;
4−[[3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチレン]ジヒドロ−2−メチル−2H−1,2−オキサジン−3(4H)−オン;
6−ジオキソ−9H−プリン−8−イル−ケイ皮酸;
4−[4−(メチル)−5−スルホニルフェニル]−3−フェニル−2(5H)−フラノン;
4−(5−メチル−3−フェニル−4−イソオキサゾリル);
2−(6−メチルピリド−3−イル)−3−(4−メチルスルホニルフェニル)−5−クロロピリジン;
4−[5−(4−メチルフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−1−イル];
N−[[4−(5−メチル−3−フェニル−4−イソオキサゾリル)フェニル]スルホニル];
4−[5−(3−フルオロ−4−メトキシフェニル)−3−ジフルオロメチル−1H−ピラゾール−1−イル]ベンゼンスルホンアミド;
(S)−6,8−ジクロロ−2−(トリフルオロメチル)−2H−1−ベンゾピラン−3−カルボン酸;
2−(3,4−ジフルオロフェニル)−4−(3−ヒドロキシ−3−メチルブトキシ)−5−[4−(メチルスルホニル)フェニル]−3(2H)−ピリドザイノン;
2−トリフルオロメチル−3H−ナフト[2,1−b]ピラン−3−カルボン酸;
6−クロロ−7−(1,1−ジメチルエチル)−2−トリフルオロメチル−2H−1−ベンゾピラン−3−カルボン酸;及び
[2−(2,4−ジクロロ−6−エチル−3,5−ジメチル−フェニルアミノ)−5−プロピル−フェニル]−酢酸からなる群より選択される、請求項1の組成物。 A cyclooxygenase-2 selective inhibitor, a pharmaceutically acceptable salt, isomer, or prodrug thereof:
3-[(3-chloro-phenyl)-(4-methanesulfonyl-phenyl) -methylene] -dihydro-furan-2-one;
8-acetyl-3- (4-fluorophenyl) -2- (4-methylsulfonyl) phenyl-imidazo (1,2-a);
5,5-dimethyl-4- (4-methylsulfonyl) phenyl-3-phenyl-2- (5H) -furanone;
5- (4-fluorophenyl) -1- [4- (methylsulfonyl) phenyl] -3- (trifluoromethyl) pyrazole;
4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] -1-phenyl-3- (trifluoromethyl) pyrazole;
4- (5- (4-chlorophenyl) -3- (4-methoxyphenyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (3,5-bis (4-methylphenyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (5- (4-chlorophenyl) -3-phenyl-1H-pyrazol-1-yl) benzenesulfonamide;
4- (3,5-bis (4-methoxyphenyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (5- (4-chlorophenyl) -3- (4-methylphenyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (5- (4-chlorophenyl) -3- (4-nitrophenyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (5- (4-chlorophenyl) -3- (5-chloro-2-thienyl) -1H-pyrazol-1-yl) benzenesulfonamide;
4- (4-chloro-3,5-diphenyl-1H-pyrazol-1-yl) benzenesulfonamide;
4- [5- (4-chlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5-phenyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-fluorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-methoxyphenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-chlorophenyl) -3- (difluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-methylphenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [4-chloro-5- (4-chlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [3- (difluoromethyl) -5- (4-methylphenyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [3- (difluoromethyl) -5-phenyl-1H-pyrazol-1-yl] benzenesulfonamide;
4- [3- (difluoromethyl) -5- (4-methoxyphenyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [3-cyano-5- (4-fluorophenyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [3- (difluoromethyl) -5- (3-fluoro-4-methoxyphenyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (3-Fluoro-4-methoxyphenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [4-chloro-5-phenyl-1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-chlorophenyl) -3- (hydroxymethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4- (N, N-dimethylamino) phenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
5- (4-fluorophenyl) -6- [4- (methylsulfonyl) phenyl] spiro [2.4] hept-5-ene;
4- [6- (4-fluorophenyl) spiro [2.4] hept-5-en-5-yl] benzenesulfonamide;
6- (4-Fluorophenyl) -7- [4- (methylsulfonyl) phenyl] spiro [3.4] oct-6-ene;
5- (3-chloro-4-methoxyphenyl) -6- [4- (methylsulfonyl) phenyl] spiro [2.4] hept-5-ene;
4- [6- (3-Chloro-4-methoxyphenyl) spiro [2.4] hept-5-en-5-yl] benzenesulfonamide;
5- (3,5-dichloro-4-methoxyphenyl) -6- [4- (methylsulfonyl) phenyl] spiro [2.4] hept-5-ene;
5- (3-chloro-4-fluorophenyl) -6- [4- (methylsulfonyl) phenyl] spiro [2.4] hept-5-ene;
4- [6- (3,4-dichlorophenyl) spiro [2.4] hept-5-en-5-yl] benzenesulfonamide;
2- (3-chloro-4-fluorophenyl) -4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) thiazole;
2- (2-chlorophenyl) -4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) thiazole;
5- (4-fluorophenyl) -4- (4-methylsulfonylphenyl) -2-methylthiazole;
4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) -2-trifluoromethylthiazole;
4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) -2- (2-thienyl) thiazole;
4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) -2-benzylaminothiazole;
4- (4-fluorophenyl) -5- (4-methylsulfonylphenyl) -2- (1-propylamino) thiazole;
2-[(3,5-dichlorophenoxy) methyl-4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] thiazole;
5- (4-fluorophenyl) -4- (4-methylsulfonylphenyl) -2-trifluoromethylthiazole;
1-methylsulfonyl-4- [1,1-dimethyl-4- (4-fluorophenyl) cyclopenta-2,4-dien-3-yl] benzene;
4- [4- (4-fluorophenyl) -1,1-dimethylcyclopenta-2,4-dien-3-yl] benzenesulfonamide;
5- (4-fluorophenyl) -6- [4- (methylsulfonyl) phenyl] spiro [2.4] hepta-4,6-diene;
4- [6- (4-fluorophenyl) spiro [2.4] hepta-4,6-dien-5-yl] benzenesulfonamide;
6- (4-Fluorophenyl) -2-methoxy-5- [4- (methylsulfonyl) phenyl] -pyridine-3-carbonitrile;
2-bromo-6- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] -pyridine-3-carbonitrile;
6- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] -2-phenyl-pyridine-3-carbonitrile;
4- [2- (4-methylpyridin-2-yl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
4- [2- (5-methylpyridin-3-yl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
4- [2- (2-methylpyridin-3-yl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
3- [1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazol-2-yl] pyridine;
2- [1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazol-2-yl] pyridine;
2-methyl-4- [1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazol-2-yl] pyridine;
2-methyl-6- [1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazol-2-yl] pyridine;
4- [2- (6-methylpyridin-3-yl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
2- (3,4-difluorophenyl) -1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazole;
4- [2- (4-methylphenyl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
2- (4-chlorophenyl) -1- [4- (methylsulfonyl) phenyl] -4-methyl-1H-imidazole;
2- (4-chlorophenyl) -1- [4- (methylsulfonyl) phenyl] -4-phenyl-1H-imidazole;
2- (4-chlorophenyl) -4- (4-fluorophenyl) -1- [4- (methylsulfonyl) phenyl] -1H-imidazole;
2- (3-Fluoro-4-methoxyphenyl) -1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazole;
1- [4- (methylsulfonyl) phenyl] -2-phenyl-4-trifluoromethyl-1H-imidazole;
2- (4-methylphenyl) -1- [4- (methylsulfonyl) phenyl] -4-trifluoromethyl-1H-imidazole;
4- [2- (3-chloro-4-methylphenyl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
2- (3-fluoro-5-methylphenyl) -1- [4- (methylsulfonyl) phenyl] -4- (trifluoromethyl) -1H-imidazole;
4- [2- (3-Fluoro-5-methylphenyl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
2- (3-methylphenyl) -1- [4- (methylsulfonyl) phenyl] -4-trifluoromethyl-1H-imidazole;
4- [2- (3-methylphenyl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
1- [4- (methylsulfonyl) phenyl] -2- (3-chlorophenyl) -4-trifluoromethyl-1H-imidazole;
4- [2- (3-chlorophenyl) -4-trifluoromethyl-1H-imidazol-1-yl] benzenesulfonamide;
4- [2-phenyl-4-trifluoromethyl-1H-imidazol-1-yl] benzenesulfonamide;
4- [2- (4-methoxy-3-chlorophenyl) -4-trifluoromethyl-1H-imidazol-1-yl] benzenesulfonamide;
1-allyl-4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -5- (trifluoromethyl) -1H-pyrazole;
4- [1-ethyl-4- (4-fluorophenyl) -5- (trifluoromethyl) -1H-pyrazol-3-yl] benzenesulfonamide;
N-phenyl- [4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -5- (trifluoromethyl) -1H-pyrazol-1-yl] acetamide;
[4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -5- (trifluoromethyl) -1H-pyrazol-1-yl] ethyl acetate;
4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -1- (2-phenylethyl) -1H-pyrazole;
4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -1- (2-phenylethyl) -5- (trifluoromethyl) pyrazole;
1-ethyl-4- (4-fluorophenyl) -3- [4- (methylsulfonyl) phenyl] -5- (trifluoromethyl) -1H-pyrazole;
5- (4-fluorophenyl) -4- (4-methylsulfonylphenyl) -2-trifluoromethyl-1H-imidazole;
4- [4- (methylsulfonyl) phenyl] -5- (2-thiophenyl) -2- (trifluoromethyl) -1H-imidazole;
5- (4-fluorophenyl) -2-methoxy-4- [4- (methylsulfonyl) phenyl] -6- (trifluoromethyl) pyridine;
2-ethoxy-5- (4-fluorophenyl) -4- [4- (methylsulfonyl) phenyl] -6- (trifluoromethyl) pyridine;
5- (4-fluorophenyl) -4- [4- (methylsulfonyl) phenyl] -2- (2-propynyloxy) -6- (trifluoromethyl) pyridine;
2-bromo-5- (4-fluorophenyl) -4- [4- (methylsulfonyl) phenyl] -6- (trifluoromethyl) pyridine;
4- [2- (3-chloro-4-methoxyphenyl) -4,5-difluorophenyl] benzenesulfonamide;
1- (4-fluorophenyl) -2- [4- (methylsulfonyl) phenyl] benzene;
5-difluoromethyl-4- (4-methylsulfonylphenyl) -3-phenylisoxazole;
4- [3-ethyl-5-phenylisoxazol-4-yl] benzenesulfonamide;
4- [5-difluoromethyl-3-phenylisoxazol-4-yl] benzenesulfonamide;
4- [5-hydroxymethyl-3-phenylisoxazol-4-yl] benzenesulfonamide;
4- [5-methyl-3-phenyl-isoxazol-4-yl] benzenesulfonamide;
1- [2- (4-fluorophenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (4-fluoro-2-methylphenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (4-chlorophenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (2,4-dichlorophenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (4-trifluoromethylphenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (4-methylthiophenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (4-fluorophenyl) -4,4-dimethylcyclopenten-1-yl] -4- (methylsulfonyl) benzene;
4- [2- (4-fluorophenyl) -4,4-dimethylcyclopenten-1-yl] benzenesulfonamide;
1- [2- (4-chlorophenyl) -4,4-dimethylcyclopenten-1-yl] -4- (methylsulfonyl) benzene;
4- [2- (4-chlorophenyl) -4,4-dimethylcyclopenten-1-yl] benzenesulfonamide;
4- [2- (4-fluorophenyl) cyclopenten-1-yl] benzenesulfonamide;
4- [2- (4-chlorophenyl) cyclopenten-1-yl] benzenesulfonamide;
1- [2- (4-methoxyphenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
1- [2- (2,3-difluorophenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
4- [2- (3-fluoro-4-methoxyphenyl) cyclopenten-1-yl] benzenesulfonamide;
1- [2- (3-chloro-4-methoxyphenyl) cyclopenten-1-yl] -4- (methylsulfonyl) benzene;
4- [2- (3-chloro-4-fluorophenyl) cyclopenten-1-yl] benzenesulfonamide;
4- [2- (2-methylpyridin-5-yl) cyclopenten-1-yl] benzenesulfonamide;
2- [4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] oxazol-2-yl] -2-benzyl-ethyl acetate;
2- [4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] oxazol-2-yl] acetic acid;
2- (tert-butyl) -4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] oxazole;
4- (4-fluorophenyl) -5- [4- (methylsulfonyl) phenyl] -2-phenyloxazole;
4- (4-fluorophenyl) -2-methyl-5- [4- (methylsulfonyl) phenyl] oxazole;
4- [5- (3-fluoro-4-methoxyphenyl) -2-trifluoromethyl-4-oxazolyl] benzenesulfonamide;
6-chloro-7- (1,1-dimethylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
6-chloro-8-methyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid;
5,5-dimethyl-3- (3-fluorophenyl) -4-methylsulfonyl-2 (5H) -furanone;
6-chloro-2-trifluoromethyl-2H-1-benzothiopyran-3-carboxylic acid;
4- [5- (4-chlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (4-methylphenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
4- [5- (3-Fluoro-4-methoxyphenyl) -3- (difluoromethyl) -1H-pyrazol-1-yl] benzenesulfonamide;
3- [1- [4- (methylsulfonyl) phenyl] -4-trifluoromethyl-1H-imidazol-2-yl] pyridine;
2-methyl-5- [1- [4- (methylsulfonyl) phenyl] -4-trifluoromethyl-1H-imidazol-2-yl] pyridine;
4- [2- (5-methylpyridin-3-yl) -4- (trifluoromethyl) -1H-imidazol-1-yl] benzenesulfonamide;
4- [5-methyl-3-phenylisoxazol-4-yl] benzenesulfonamide;
4- [5-hydroxymethyl-3-phenylisoxazol-4-yl] benzenesulfonamide;
[2-trifluoromethyl-5- (3,4-difluorophenyl) -4-oxazolyl] benzenesulfonamide;
4- [2-methyl-4-phenyl-5-oxazolyl] benzenesulfonamide;
4- [5- (2-fluoro-4-methoxyphenyl) -2-trifluoromethyl-4-oxazolyl] benzenesulfonamide;
[2- (2-Chloro-6-fluoro-phenylamino) -5-methyl-phenyl] -acetic acid;
N- (4-nitro-2-phenoxy-phenyl) -methanesulfonamide or nimesulide;
N- [6- (2,4-difluoro-phenoxy) -1-oxo-indan-5-yl] -methanesulfonamide;
N- [6- (2,4-difluoro-phenylsulfanyl) -1-oxo-1H-inden-5-yl] -methanesulfonamide sodium salt;
N- [5- (4-Fluoro-phenylsulfanyl) -thiophen-2-yl] -methanesulfonamide;
3- (3,4-difluoro-phenoxy) -4- (4-methanesulfonyl-phenyl) -5-methyl-5- (2,2,2-trifluoroethyl) -5H-furan-2-one;
(5Z) -2-amino-5-[[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methylene-4 (5H) -thiazolone;
N- [3- (formylamino) -4-oxo-6-phenoxy-4H-1-benzopyran-7-yl] -methanesulfonamide;
(6aR, 10aR) -3- (1,1-dimethylheptyl) -6a, 7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo [b, d] pyran-9-carvone acid;
4-[[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methylene] dihydro-2-methyl-2H-1,2-oxazin-3 (4H) -one;
6-Dioxo-9H-purin-8-yl-cinnamic acid;
4- [4- (methyl) -5-sulfonylphenyl] -3-phenyl-2 (5H) -furanone;
4- (5-methyl-3-phenyl-4-isoxazolyl);
2- (6-methylpyrid-3-yl) -3- (4-methylsulfonylphenyl) -5-chloropyridine;
4- [5- (4-methylphenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl];
N-[[4- (5-Methyl-3-phenyl-4-isoxazolyl) phenyl] sulfonyl];
4- [5- (3-Fluoro-4-methoxyphenyl) -3-difluoromethyl-1H-pyrazol-1-yl] benzenesulfonamide;
(S) -6,8-dichloro-2- (trifluoromethyl) -2H-1-benzopyran-3-carboxylic acid;
2- (3,4-difluorophenyl) -4- (3-hydroxy-3-methylbutoxy) -5- [4- (methylsulfonyl) phenyl] -3 (2H) -pyridosainone;
2-trifluoromethyl-3H-naphtho [2,1-b] pyran-3-carboxylic acid;
6-chloro-7- (1,1-dimethylethyl) -2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid; and [2- (2,4-dichloro-6-ethyl-3,5 2. The composition of claim 1 selected from the group consisting of -dimethyl-phenylamino) -5-propyl-phenyl] -acetic acid.
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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US39329702P | 2002-07-02 | 2002-07-02 | |
US39329602P | 2002-07-02 | 2002-07-02 | |
US39317202P | 2002-07-02 | 2002-07-02 | |
US39313602P | 2002-07-02 | 2002-07-02 | |
US39319902P | 2002-07-02 | 2002-07-02 | |
US39326902P | 2002-07-02 | 2002-07-02 | |
US39325802P | 2002-07-02 | 2002-07-02 | |
PCT/US2003/020558 WO2004004833A1 (en) | 2002-07-02 | 2003-06-30 | Use of cyclooxygenase-2 selective inhibitors and thrombolytic agents for the treatment or prevention of a vaso-occlusive event |
Publications (2)
Publication Number | Publication Date |
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JP2005535657A JP2005535657A (en) | 2005-11-24 |
JP2005535657A5 true JP2005535657A5 (en) | 2006-08-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2004519699A Withdrawn JP2005535657A (en) | 2002-07-02 | 2003-06-30 | Use of cyclooxygenase-2 selective inhibitor and thrombolytic agent for treatment or prevention of vascular occlusion event |
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Country | Link |
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US (1) | US20040063697A1 (en) |
EP (1) | EP1536863A1 (en) |
JP (1) | JP2005535657A (en) |
AU (1) | AU2003248759A1 (en) |
BR (1) | BR0312402A (en) |
CA (1) | CA2491479A1 (en) |
MX (1) | MXPA05000259A (en) |
WO (1) | WO2004004833A1 (en) |
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US9209956B2 (en) | 2005-08-22 | 2015-12-08 | Qualcomm Incorporated | Segment sensitive scheduling |
Family Cites Families (17)
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US4853330A (en) * | 1983-04-07 | 1989-08-01 | Genentech, Inc. | Human tissue plasminogen activator |
US4477043A (en) * | 1982-12-15 | 1984-10-16 | The United States Of America As Represented By The Secretary Of The Air Force | Biodynamic resistant control stick |
US5061813A (en) * | 1990-04-02 | 1991-10-29 | E. R. Squibb & Sons, Inc. | Substituted cyanoimino benzopyranes |
US5276168A (en) * | 1990-06-18 | 1994-01-04 | E. R. Squibb & Sons, Inc. | Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents |
US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
US5344991A (en) * | 1993-10-29 | 1994-09-06 | G.D. Searle & Co. | 1,2 diarylcyclopentenyl compounds for the treatment of inflammation |
US5434178A (en) * | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
US5633272A (en) * | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
US5510368A (en) * | 1995-05-22 | 1996-04-23 | Merck Frosst Canada, Inc. | N-benzyl-3-indoleacetic acids as antiinflammatory drugs |
US5939790A (en) * | 1996-04-09 | 1999-08-17 | Altera Corporation | Integrated circuit pad structures |
IL125849A (en) * | 1996-04-12 | 2003-10-31 | Searle & Co | Substituted benzenesulfonamide derivatives, their preparation and pharmaceutical compositions comprising them |
US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
US6136804A (en) * | 1998-03-13 | 2000-10-24 | Merck & Co., Inc. | Combination therapy for treating, preventing, or reducing the risks associated with acute coronary ischemic syndrome and related conditions |
US20030153801A1 (en) * | 2001-05-29 | 2003-08-14 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease |
-
2003
- 2003-06-30 WO PCT/US2003/020558 patent/WO2004004833A1/en not_active Application Discontinuation
- 2003-06-30 CA CA002491479A patent/CA2491479A1/en not_active Abandoned
- 2003-06-30 JP JP2004519699A patent/JP2005535657A/en not_active Withdrawn
- 2003-06-30 US US10/610,085 patent/US20040063697A1/en not_active Abandoned
- 2003-06-30 AU AU2003248759A patent/AU2003248759A1/en not_active Abandoned
- 2003-06-30 MX MXPA05000259A patent/MXPA05000259A/en not_active Application Discontinuation
- 2003-06-30 EP EP03763058A patent/EP1536863A1/en not_active Withdrawn
- 2003-06-30 BR BR0312402-9A patent/BR0312402A/en not_active IP Right Cessation
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